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Cycling the Heel of Italy - Alberobello to Lecce

0044 1606 720199

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  • Holiday code
    C07PI
  • Holiday type
    Self-guided cycling
  • Duration
    7 nights
  • Accommodation
    hotel-to-hotel
    , and
  • Activity level
  • From $2049per person, tour only
  • Departures
    Saturdays, Mondays and Thursdays from 10 Jun '23 to 28 Oct '24
  • What your holiday price includes
  • 7 nights hotel-to-hotel accommodation in a mix of , and hotels
  • All breakfasts and 1 evening meal
  • Management by your local Headwater-appointed agent
  • Headwater navigation app
  • Bike hire included
  • Luggage transfers between hotels
  • Optional Upgrades
  • Electric bikes available
  • Tandems available
  • Suitable for
  • Solo travellers
  • Couples
  • Excellent choice for
  • Food lovers, wine lovers, art & history, swimming opportunities, vegetarian meals, coastal routes
      from 17 reviews

Mr Mitchell says...
Itinerary fine. Unfortunately weather not great do not a lot to do when cycling finished
Read reviews »

Italy: Puglia

Cycling the Heel of Italy - Alberobello to Lecce

  • Alberobello's fairy-tale trulli houses
  • Olive groves, towering limestone cliffs and Roman amphitheatres
  • The white city of Ostuni, the majestic castle of Otranto and Baroque Lecce

In the heart of the Mediterranean lies Puglia, a unique landscape sandwiched between the Adriatic and Ionian seas. We explore the very best of this captivating region from our start point in Alberobello, known for its UNESCO-listed Trulli houses, to the end point in Lecce, known as the 'Florence of the South'.
The daily routes take you through the Murghe plateau, the Salento plain or along the coast. Discover a landscape of ancient olive groves, long fields of grain and vineyards. The architecture of the region takes you from the conical Trulli houses in Alberobello, the white city of Ostuni, past traditional masserie, coastal watchtowers and splendid Baroque towns. The region is filled with spectacular views; beautiful coastline and mouth-watering cuisine.
This holiday is offered with a choice of mainly 3 Star, or mainly 4 Star accommodation. The 3 Star accommodation is listed on the hotels page.



We're here to help

If you have any questions about this holiday call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com

Day-by-day itinerary



We're here to help

If you've any questions about this holiday call our sales team on 0044 1606 720199 , or email sales@headwater.com

Day 1: Arrive in Alberobello

Make your way to Alberobello, famous for its Trulli houses.

Day 2: Alberobello to Ostuni 49km/31mi

Cycle through the lush Valle d'Itria, passing more white-tipped trulli houses on the way. Boasting beautiful coastal views, the route takes you through the famous wine town of Locorotondo, regarded as one of Italy's most stunning villages. After sampling some of the local sparkling white wine, continue to the white city of Ostuni - so called for the dazzling effect of its whitewashed houses.
Breakfast included

Day 3: Ostuni to Avetrana 55km/34.5mi

Cycle through the colourful Salentinian countryside, characterized by olive groves and red soil towards the medieval towns of Oria and Manduria with their authentic historic centres.
Breakfast and evening meal included

Day 4: Avetrana to Gallipoli 60km/37.5mi

Head to Torre Colimena on the Ionian Sea, then follow the coast alongside a series of beaches and the old coastal towers of Salento. Reach Gallipoli, known as the 'Ionian Pearl' with its Old Town situated on a rocky island. Take time to wander the narrow lanes of the historic centre to discover its baroque cathedral, elegant palazzi and enticing restaurants.
Breakfast included

Day 5: Gallipoli to Santa Maria di Leuca 50km/31.5mi

Cycle towards the most southerly point of Salento at Santa Maria di Leuca, where the crystal waters of the Ionian and Adriatic Sea meet. This village is home to one of the most important lighthouses in Italy, as well as numerous villas built at the turn of the century.
Breakfast included

Day 6: Santa Maria di Leuca to Otranto 53km/33.5mi

Pedal along the south coast of the Adriatic Sea, stopping off at the famous Grotta Zinzulusa and the thermal baths of Santa Cesarea Terme. Your final destination is Otranto, the most eastern point of Italy with a stunning cathedral and Aragonese castle.
Breakfast included

Day 7: Otranto to Lecce 54km/34mi

Follow the shoreline through olive groves to the Baroque metropolis of Lecce. Known as the 'Florence of the South', Lecce is home to over 30 churches, an amphitheatre and a Roman theatre dating back to Emperor Augustus.
Breakfast included

Day 8: Leave Lecce


Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking.

To find out more call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Trullidea, Alberobello

Hair dryer icon

A unique and authentic experience staying in a trulli, a traditional 15th century Apulian stone building with conical roof.

Each trulli house is made up of a double bedroom, small bathroom with shower and living area with sofa and small kitchenette.

The trullis are located in the centre of historic Alberobello, a UNESCO world heritage site, within walking distance of cafes, restaurants and shops.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Relais Sant'Eligio, Ostuni

Hair dryer icon

The origins of Relais Sant'Eligio date back to the first half of 1500 when the Queen Bona Sforza d'Aragona imposed all coastal cities from Naples and Otranto to have a resting station. The Resting Station of Camposada in Ostuni was built along the ancient 'Via del Procaccia', the route running along the ancient walls of the White Town. Between 1630 and 1810, it became the Home of the Zevallos dukes as proved by several decorative friezes and ornaments.

The name 'Sant'Eligio' derives from the patron saint of the farriers working in the stables of 'Camposada' Resting Station. The ancient emblem highlights the evocative written in Latin language: QUISQUIS HUC VENIT HUC REDIET (if you come once, you will necessarily come back again)

The rooms at Hotel Relais Sant'Eligio are elegant and comfortable.


Find out more on the hotel website.

Masseria Strazzati, Avetrana

Masseria Strazzati is an old farm estate and is set within 100 hectares of olive groves. Your evening meal is taken at the Masseria Bosco where the pool can also be used.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Joly Park, Gallipoli

Swimming Pool IconHair dryer iconNEARBY:

Located in the centre of Gallipoli and only a short walk from Corso Roma, Hotel Joli Park is modern and comfortable.

The rooms are well equipped and contemporary. The hotels offers guests a private shuttle service to take you to and from the private beach “Lido delle Sirene”.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Terminal, Leuca

Swimming Pool IconHair dryer iconNEARBY:

Hotel Terminal is nestled among the eclectic villas, on the central nineteenth-century seafront dedicated to Cristoforo Colombo, the heart of the town, with a beautiful view on Punta Ristola and Punta Melis.

The hotel has it's own private beach that can be reached by a picturesque underpass. Rooms are comfortable and well equipped.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Albania, Otranto

Hair dryer iconNEARBY:

Located in the centre of Otranto, Hotel Albania owes its name to the majestic Albanian mountains which on a clear day offers guests breathtaking views and are visible from the hotel terrace.

Rooms are comfortable and modern.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Eos Hotel, Lecce

Hair dryer iconNEARBY:

Situated just outside of the historic town of Lecce, Hotel Eos is a modern hotel with modern facilities.

Rooms are contemporary and fully furnished.

Extending your stay

If you'd like to extend your trip with extra nights at the start or end, or if you'd like to arrange a stop off point en-route, then we recommend the following hotels.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Excelsior, Bari

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The Hotel Excelsior has large and bright rooms. There is also a bar and restaurant offering Mediterranean dishes.

Travel

Transfers can be arranged at a supplement from Bari Airport at 14:20.

Call now to speak to our specialist team at 0044 1606 720199 or email us at sales@headwater.com for enquiries or to book your trip.

Reviews

Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus an overall rating and comments about their holiday.

Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.


Mr Mitchell, 11/05/2023

Itinerary fine. Unfortunately weather not great do not a lot to do when cycling finished


Ms Turner, 19/04/2023

Excellent. Superb trip, well organised.


Mrs Butler, 02/10/2022

Super. Cycling tour. Everything we needed was provided by friendly and efficient service. Highly recommended.


Mrs Kennedy, 16/07/2022

A great active holiday where you travel through different landscapes to arrive in interesting towns with lovely hotels.


Ms Hall, 11/07/2022

It was lovely to arrive at the end of a ride in the little towns of Puglia, all different and charming. Some of the cycling was really spectacular, particularly along the coast. I was pleased to have an e-bike as the temperature was way over 30 degrees everyday at the end of May. As someone not very tech-savvy, I needed help with the navigation app. Remember to download last-minute adjustments just before you go!


Mr Scott, 02/07/2022

Great route. Varying quality of hotels. Poor bikes. Expensive for what we got.


Mrs Davidson, 30/06/2022

This cycling route through Puglia is a stunningly beautiful one - particularly in late May when the poppies and other wild flowers were in full bloom; the weather warm but not scorching and not too busy with other tourists. This was the first Headwater cycling trip I have done without 'stay put' days, and the overall mileage each day (at leisurely pace) did mean there was little spare time for sightseeing. However, it was absolutely worth the effort to visit each of the locations - they were wonderfully varied and I wouldn't have wanted to miss out on any of them!

One of the days involves taking a train - it's worth noting that not all the trains allow bikes, and we were lucky to have had help lifting up the bikes into the hanging racks on the train - a tricky manouevre for the vertically challenged!


Mrs Haddock, 29/06/2022

A great itinerary, a lot of variation in level of challenge.


Mr Rhodes, 02/06/2022

A very enjoyable holiday, staying at interesting places in good accommodation. We would certainly book with Headwater again for a cycling holiday


Mr Becket, 19/05/2022

Fantastic way to see the glorious countryside, towns, cities and natural beauty of Puglia. Well organised, good bikes, good accommodation and we think the best way to immerse yourself in a location. As firstimers with Headwater would highly recommend to anyone.


Mrs Dudgeon, 19/05/2022

Excellent. the App was easy to use for middle aged people who usually ask their children to work this kind of thing out. The Headwater emails were well timed and informative and when you passed us on to Gulia cycle tours, they were equally as efficient. The route was fantastic, the hotels just ideal for this holiday. The people we met from Puglia Tours delightful. We had 2 potentially big problems - A) one of our parties' bags didn't arrive from England on our flight. So we logged a missing bag form at Barri airport but it was difficult with language barrier and not knowing where we would be if and when the bag might catch up with us. Headwater were amazing and the bag caught us up 2 days later. And the driver from Puglio Tours took us from Barri airport to a hypermarket ( thank god open on a Sunday pm) to buy essentials. We also had a problem with a bike and again - fantastic backup and all sorted. Best holiday & when probs occurred the finest back up


Mr Hrouda, 24/04/2022

An exceptional route - everything had been thought of. The first day is a long distance so it might be off putting for those who don’t cycle long distances regularly. The food everywhere is of a fantastically high standard. We recommend Le Bubbole in Matera, La Cantina in Alberobello and The Dish in Ostuni. Booking in advance recommended.


Mr WADE, 04/11/2021

Our holiday was a celebration for our 30th wedding anniversary. In order to be consistent with the previous thirty years of marriage I left the planning until the last minute. I contacted Headwaters barely two weeks before the half term started yet they were able , as ever, to provide a first class service which totally met what we were looking for. From the moment we landed, where we met Mimmo our agent, until our departure from our gorgeous Lecce hotel on the final morning, we encountered nothing but an amazing service wherever we visited or stayed. We loved all of the accommodation as well as the stunning routes. Puglia is indeed an astonishingly beautiful region in Italy, as evidenced by the breath taking coastal routes to Gallipoli and Otranto. Likewise the climb to the hilltop town of Ostuni, as well the town itself, was simply stunning. I am running out of synonyms for brilliant but that is the adjective that I want to use to describe the everything about the trip. Thank you.


Mr HALL, 19/10/2021

It was a well thought-out itinerary which took in the high-lights of Puglia - rural rides to beautiful hill-top towns and coastal rides with lovely views over the Mediterranean.


Mr Paul, 13/11/2019

Excellent holiday with good hotels, great scenery and realistic riding days for the described activity level. The bikes were excellent and comfortable.


Mr Partridge, 30/10/2019

This was our first cycling holiday (we are in our seventies) We had the most enjoyable time, meeting up with fellow cyclist from other countries on route

The towns we stayed in and the hotel were all very good. The cycling was almost all on quiet roads. We would certainly like to book another trip. Mary and Tim


Mrs REDSHAW, 00/00/0000

The cycling was fun and the app was generally easy to use though you should take an external battery pack. My phone was 3 years old and you need to set the screen to be quite bright so it uses up power quite quickly. The hotels that we used were all 3* but were comfortable. All hotels provided excellent breakfasts. We went in early May which is described as part of the holiday season but we found most places still closed so stopping off along the way wasn't as easy as we expected. One thing that we were really surprised by was the cost of transfers to and from the airport that Headwater wished to charge. Something like 240 from Bari to Arborobella (we caught a bus for 8 euros, and over 400 from Lecce back to Bari ( we caught the train for 24 euros). We hadn't been cycling for some years before booking this holiday but we practised for 5 weeks before going and we were fine.



Dates and prices

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday.

This 7 night self-guided cycling holiday includes:

Hotel-to-hotel accommodation in a mix of , and hotels

All breakfasts and 1 evening meal

Management by your local Headwater-appointed agent

Headwater navigation app for your smartphone

Bike hire

Luggage transfers between hotels


How to book:

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' or 'check availability' button below.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'check availability' button below.

  • Jun 2023
  • Jul 2023
  • Aug 2023
  • Sep 2023
  • Oct 2023
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  • Oct 2024
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8th Jun 2023 US$2249 US$286 Tour only: US$2249
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31st Aug 2023 US$2379 US$286 Tour only: US$2379
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2nd Sep 2023 US$2279 US$286 Tour only: US$2279
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11th Sep 2023 US$2279 US$286 Tour only: US$2279
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14th Sep 2023 US$2279 US$286 Tour only: US$2279
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16th Sep 2023 US$2279 US$286 Tour only: US$2279
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2nd Oct 2023 US$2149 US$286 Tour only: US$2149
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21st Mar 2024 US$2049 US$286 Tour only: US$2049
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2nd May 2024 US$2399 US$286 Tour only: US$2399
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25th May 2024 US$2399 US$286 Tour only: US$2399
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1st Jun 2024 US$2399 US$286 Tour only: US$2399
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DepartingTour only Prices   Single supplement
1st Jul 2024 US$2549 US$286 Tour only: US$2549
Single supp: US$286
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Check availability
4th Jul 2024 US$2549 US$286 Tour only: US$2549
Single supp: US$286
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Check availability
6th Jul 2024 US$2549 US$286 Tour only: US$2549
Single supp: US$286
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Check availability
8th Jul 2024 US$2549 US$286 Tour only: US$2549
Single supp: US$286
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Check availability
11th Jul 2024 US$2549 US$286 Tour only: US$2549
Single supp: US$286
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Check availability
13th Jul 2024 US$2549 US$286 Tour only: US$2549
Single supp: US$286
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Check availability
15th Jul 2024 US$2549 US$286 Tour only: US$2549
Single supp: US$286
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Check availability
18th Jul 2024 US$2549 US$286 Tour only: US$2549
Single supp: US$286
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Check availability
20th Jul 2024 US$2549 US$286 Tour only: US$2549
Single supp: US$286
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Check availability
22nd Jul 2024 US$2549 US$286 Tour only: US$2549
Single supp: US$286
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Check availability
DepartingTour only Prices   Single supplement
31st Aug 2024 US$2549 US$286 Tour only: US$2549
Single supp: US$286
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Check availability
DepartingTour only Prices   Single supplement
2nd Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
5th Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
7th Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
9th Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
12th Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
14th Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
16th Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
19th Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
21st Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
23rd Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
26th Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
28th Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
30th Sep 2024 US$2449 US$286 Tour only: US$2449
Single supp: US$286
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Check availability
DepartingTour only Prices   Single supplement
3rd Oct 2024 US$2279 US$286 Tour only: US$2279
Single supp: US$286
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Check availability
5th Oct 2024 US$2279 US$286 Tour only: US$2279
Single supp: US$286
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Check availability
7th Oct 2024 US$2279 US$286 Tour only: US$2279
Single supp: US$286
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Check availability
10th Oct 2024 US$2279 US$286 Tour only: US$2279
Single supp: US$286
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Check availability
12th Oct 2024 US$2279 US$286 Tour only: US$2279
Single supp: US$286
Check availability
Check availability
14th Oct 2024 US$2279 US$286 Tour only: US$2279
Single supp: US$286
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Check availability
17th Oct 2024 US$2279 US$286 Tour only: US$2279
Single supp: US$286
Check availability
Check availability
19th Oct 2024 US$2279 US$286 Tour only: US$2279
Single supp: US$286
Check availability
Check availability
21st Oct 2024 US$2279 US$286 Tour only: US$2279
Single supp: US$286
Check availability
Check availability
24th Oct 2024 US$2279 US$286 Tour only: US$2279
Single supp: US$286
Check availability
Check availability
26th Oct 2024 US$2279 US$286 Tour only: US$2279
Single supp: US$286
Check availability
Check availability
28th Oct 2024 US$2279 US$286 Tour only: US$2279
Single supp: US$286
Check availability
Check availability

The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.

Holiday details

Solo travellers
Please call for details and prices

Children
This holiday is unsuitable for children.

Holiday type
Self-guided cycling Managed locally by Headwater appointed agent.

Departures
Saturdays, Mondays and Thursdays from 8th Jun 2023 to 28th Oct 2024, for 7 nights. All dates are subject to availability, please contact us to check.

Meals
All breakfasts and 1 evening meal

Electric bikes
It is possible to hire electric bikes for this holiday at a supplement of £256 per person. As these are available on a first come first served basis, we recommend early booking to avoid disappointment.

Tandems
It is possible to hire tandem bikes for this holiday at a supplement of £182 per bike. As these are available on a first come first served basis, we recommend early booking to avoid disappointment.

Other details
This holiday is also available with mainly 4 Star accommodation.

Tailor-made travel

Tour only

Transfers can be arranged at a supplement from Bari Airport at 14:20.

How to book

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' button above.

If you need further information before you book simply complete our Holiday Enquiry Form and a member of our sales team will get back to you.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'Check availability' button below.

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